NO122701B - - Google Patents
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- NO122701B NO122701B NO167038A NO16703867A NO122701B NO 122701 B NO122701 B NO 122701B NO 167038 A NO167038 A NO 167038A NO 16703867 A NO16703867 A NO 16703867A NO 122701 B NO122701 B NO 122701B
- Authority
- NO
- Norway
- Prior art keywords
- peroxydicarbonate
- peroxydicarbonates
- bis
- cycloalkyl
- dicyclohexyl
- Prior art date
Links
- BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical class C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003505 polymerization initiator Substances 0.000 claims description 2
- -1 N-substituted methacrylamides Chemical class 0.000 description 7
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 2
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- IWVJLGPDBXCTDA-UHFFFAOYSA-N cyclohexyl carbonochloridate Chemical compound ClC(=O)OC1CCCCC1 IWVJLGPDBXCTDA-UHFFFAOYSA-N 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/32—Peroxy compounds the —O—O— group being bound between two >C=O groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
Description
Nye 4-substituerte dicyclohexyl-peroxydicarbonater for anvendelse som oxydasjonsmidler og som polymerisasjonsinitiatorer. New 4-substituted dicyclohexyl-peroxydicarbonates for use as oxidizing agents and as polymerization initiators.
Foreliggende oppfinnelse angår ^-substituerte dicyclohexylper-oxydicarbonater for anvendelse som oxydasjonsmidler og som initiatorer ved polymerisering av polymeriserbare umettede monomere. The present invention relates to ^-substituted dicyclohexylperoxydicarbonates for use as oxidizing agents and as initiators in the polymerization of polymerizable unsaturated monomers.
Det er kjent at diisopropyl-, di-n-butyl- og dicyclohexyl-peroxydicarbonater er effektive som initiatorer ved polymerisering av polymeriserbare umettede monomere. Typiske forbindelser som kan polymeriseres, er de som inneholder vinylgrupper, såsom vinylklorid, vinylidenklorid, vinylbromid, acrylamid, N-substituerte methacrylamid-er, acrylnitril, vinylacetat og methylmethacrylat og forbindelser som inneholder allylgrupper, såsom allylacetat og diethylenglycol-bis-(allylcarbonat) samt andre polymeriserbare forbindelser, såsom ethylen. Kfr.kl. 12 o-27 Diisopropyl, di-n-butyl and dicyclohexyl peroxydicarbonates are known to be effective as initiators in the polymerization of polymerizable unsaturated monomers. Typical compounds that can be polymerized are those containing vinyl groups, such as vinyl chloride, vinylidene chloride, vinyl bromide, acrylamide, N-substituted methacrylamides, acrylonitrile, vinyl acetate and methyl methacrylate and compounds containing allyl groups, such as allyl acetate and diethylene glycol bis-(allyl carbonate) as well as other polymerizable compounds, such as ethylene. Kfr. at 12 o-27
De ovennevnte peroxydicarbonater er imidlertid beheftet medHowever, the above-mentioned peroxydicarbonates are affected
den ulempe at-de ' spaltes "ved romtemperatur og ved noe hbyere tem-peraturer undergår eksplosjonsartet spaltning. Som folge av disse særegenskaper må disse peroxydicarbonater håndteres, transporteres og lagres i nedkjolt tilstand. the disadvantage that they "decompose" at room temperature and at slightly higher temperatures undergo explosive decomposition. As a result of these special properties, these peroxydicarbonates must be handled, transported and stored in a cooled state.
Det har nu overraskende vist seg at hittil ukjente ^-substituerte dicyclohexyl-peroxydicarbonater av strukturformelen: 0 0 It has now surprisingly been shown that hitherto unknown ^-substituted dicyclohexyl-peroxydicarbonates of the structural formula: 0 0
R—( ) O—C— 0_0 _ C—0—/ \ R R—( ) O—C— 0_0 _ C—0—/ \ R
hvor R betyr et cycloalkyl-radikål med ^ - 8 carbonatomer, et alkyl-radikal med 3 - 9 carbonatomer, eller et cycloalkyl-alkyl-radikal med totalt 7-12 carbonatomer, hvorav 5 - 8 i cycloalkylringen, idet alkyl- og cycloalkyl-alkyl-radikalet er bundet til cyclohexanringen over et sekundært eller tertiært carbonatom,er stabile ved romtemperatur slik at det ikke er nodvendig å kjole dem eller stabilisere dem på annen måte under transport og/eller lagring. where R means a cycloalkyl radical with ^ - 8 carbon atoms, an alkyl radical with 3 - 9 carbon atoms, or a cycloalkyl-alkyl radical with a total of 7-12 carbon atoms, of which 5 - 8 in the cycloalkyl ring, the alkyl and cycloalkyl the alkyl radical is attached to the cyclohexane ring via a secondary or tertiary carbon atom, are stable at room temperature so that it is not necessary to coat them or otherwise stabilize them during transport and/or storage.
De nye substituerte dicyclohexyl-peroxydicarbonater er faste stoffer ved romtemperatur, og de kan anvendes som oxydasjonsmidler ved bleking av mel, som torkemidler for linfroolje, treolje, soya-bonneolje og andre oljer og som initiatorer ved polymerisering av polymeriserbare umettede monomere inneholdende vinylgrupper, så- The new substituted dicyclohexyl-peroxydicarbonates are solids at room temperature, and they can be used as oxidizing agents in the bleaching of flour, as drying agents for linseed oil, wood oil, soybean oil and other oils and as initiators in the polymerization of polymerizable unsaturated monomers containing vinyl groups, so-
som vinylklorid, vinylidenklorid, vinylbromid, acry-lamid, N-substituerte methacrylamidér, acrylonitril, vinylacetat og methylmethacrylat eller forbindelser inneholdende allylgrupper, såsom allylacetat og diethylenglycol-bis-(allylcarbonat) og andre polymeriserbare forbindelser, såsom ethylen. such as vinyl chloride, vinylidene chloride, vinyl bromide, acrylamide, N-substituted methacrylamides, acrylonitrile, vinyl acetate and methyl methacrylate or compounds containing allyl groups, such as allyl acetate and diethylene glycol bis-(allyl carbonate) and other polymerizable compounds, such as ethylene.
Som initiatorer ved polymerisering av vinylklorid er de<!>+-substituerte dicyclohexyl-peroxydicarbonater mer effektive i ekvi-valente molare mengder enn de hittil anvendte peroxydicarbonater, hvilket er fordelaktig fra et okonomisk synspunkt. Foretrukne dicyclohexyl-peroxydicarbonater fordi de er kommersielt tilgjengelige pro-dukter og således okonomisk fordelaktige, er bis-(^-isopropylcyclo-hexyl)-peroxydicarbonat, bis-(^-tert.butylcyclohexyl)-peroxydicarbonat, bis-(^--tert. amylcyclohexyl)-peroxydicarbonat, bis-C^f-cyclohexylisopropylcyclohexyl)-peroxydicarbonat og bis-(^--cyclo-hexylcyclohexyl)-peroxydicarbonat. As initiators in the polymerization of vinyl chloride, the <!>+-substituted dicyclohexyl peroxydicarbonates are more effective in equivalent molar amounts than the peroxydicarbonates used up to now, which is advantageous from an economic point of view. Preferred dicyclohexyl peroxydicarbonates because they are commercially available products and thus economically advantageous are bis-(^-isopropylcyclohexyl)-peroxydicarbonate, bis-(^-tert.butylcyclohexyl)-peroxydicarbonate, bis-(^--tert. amylcyclohexyl)-peroxydicarbonate, bis-C^f-cyclohexylisopropylcyclohexyl)-peroxydicarbonate and bis-(^--cyclohexylcyclohexyl)-peroxydicarbonate.
De<1>+-substituerte dicyclohexyl-peroxydicarbonater ifolge opp finnelsen kan fremstilles ved at man omsetter de tilsvarende halogen-formiater,fortrinnsvis klorformiatene,med en vandig, alkalisk opp-løsning av hydrogenperoxyd, fortrinnsvis en vandig opplosning av natriumhydroxyd og hydrogenperoxyd, fortrinnsvis ved en temperatur lavere enn ^5°C, og isolerer det erholdte peroxydicarbonat. The <1>+-substituted dicyclohexyl peroxydicarbonates according to the invention can be prepared by reacting the corresponding halogen formates, preferably the chloroformates, with an aqueous, alkaline solution of hydrogen peroxide, preferably an aqueous solution of sodium hydroxide and hydrogen peroxide, preferably by a temperature lower than ^5°C, and isolates the peroxydicarbonate obtained.
De nedenstående eksempler 1-5 illustrerer fremstillingen av forbindelsene ifolge oppfinnelsen. The examples 1-5 below illustrate the preparation of the compounds according to the invention.
Eksempel 1Example 1
109,2 g av en vandig 33 vekt$ NaOH-opplosning ble tilsatt under omroring til 36,7 g-vandig 50 vekt% R"202-opplosning og 675 ml vann. Blandingens temperatur ble derefter innstilt på hO°C. Det ble så tilsatt 0,69 ml av en 27 vektfo vandig opplosning av natrium-(7-ethyl-2-methylundecyl-^)-sulfat ("Tergitol" An-M som emulgerings-middel. 109.2 g of an aqueous 33 wt % NaOH solution was added with stirring to 36.7 g of an aqueous 50 wt % R" 2 O 2 solution and 675 ml of water. The temperature of the mixture was then adjusted to h0°C. It was then added 0.69 ml of a 27% by weight aqueous solution of sodium (7-ethyl-2-methylundecyl-^)-sulphate ("Tergitol" An-M) as emulsifier.
208,1 g 9^,5 %<*>+-tert.cyclohexyl-klorformiat ble under kon-tinuerlig omroring tildryppet i lopet av *+5 minutter ved kO°C og derefter 7, k g av en 50 vekt% vandig H202- opplosning. Omroringen ble derefter fortsatt i<*>+5 mintter ved hO°C. Efter avkjoling av reaksjonsblandingen til romtemperatur, ble det dannede peroxydicarbonat frafiltrert, torret ved 30° C og omkrystallisert fra pen-tan. Det ble erholdt 196 g bis-(^—tert.butylcyclohexyl)-peroxydicarbonat. Utbyttet: 92 % (beregnet på det anvendte ^-tert.butyl-cyclohexylklorformiat. 208.1 g of 9^.5%<*>+-tert.cyclohexyl-chloroformate was added dropwise with continuous stirring over the course of *+5 minutes at kO°C and then 7.k g of a 50% by weight aqueous H 2 O 2 - dissolution. Stirring was then continued for <*>+5 minutes at h0°C. After cooling the reaction mixture to room temperature, the peroxydicarbonate formed was filtered off, dried at 30° C. and recrystallized from pentane. 196 g of bis-(^-tert.butylcyclohexyl)-peroxydicarbonate were obtained. The yield: 92% (calculated on the ^-tert.butyl cyclohexyl chloroformate used.
Eksempel 2Example 2
På samme måte som beskrevet i eksempel 1 ble bis-(*+-tert.amyl-cyclohexyl)-peroxydicarbonat fremstilt ut fra ^-tert.amylcyclo-hexyl-klorformiat. In the same way as described in example 1, bis-(*+-tert.amyl-cyclohexyl)-peroxydicarbonate was prepared from .beta.-tert.amylcyclohexyl-chloroformate.
EksempelExample
På samme måte som beskrevet i eksempel 1 ble bis-( h-isopropyl-cyclohexyl)-peroxydicarbonat fremstilt ut fra ^-isopropylcyclo-hexylklorformiat. In the same way as described in example 1, bis-(h-isopropyl-cyclohexyl)-peroxydicarbonate was prepared from .beta.-isopropylcyclohexyl chloroformate.
Eksempel hExample h
På samme måte som beskrevet i eksempel 1 ble bis-(^-cyclohexylisopropylcyclohexyl)-peroxydicarbonat fremstilt ut fra cyclohexylisopropylcyclohexyl-klorformiat. In the same way as described in example 1, bis-(^-cyclohexylisopropylcyclohexyl)-peroxydicarbonate was prepared from cyclohexylisopropylcyclohexyl chloroformate.
Eksempel 5Example 5
På samme måte som beskrevet i eksempel 1 ble bis-(^-cyclo- hexylcyclohexyl)-peroxydicarbonat fremstilt ut fra ^-cyclohexyl-cyclohexyl-klorformiat. In the same way as described in example 1, bis-(^-cyclohexylcyclohexyl)-peroxydicarbonate was prepared from ^-cyclohexyl-cyclohexyl chloroformate.
Data for peroxydicarbonatene fremstilt i henhold til eksem-plene 1-5 er oppfort i den folgende tabell. Data for the peroxydicarbonates produced according to examples 1-5 are listed in the following table.
Eksempel 6 Example 6
I den hensikt å bestemme deres stabilitet ble prover av peroxydicarbonater i henhold til oppfinnelsen og av kjente peroxydicarbonater anbragt i et ror av "Pyrex"-glass og holdt ved en konstant temperatur på 30°C ved anvendelse av et bad av konstant temperatur. In order to determine their stability, samples of peroxydicarbonates according to the invention and of known peroxydicarbonates were placed in a tube of "Pyrex" glass and maintained at a constant temperature of 30°C using a constant temperature bath.
Spaltningshastigheten av peroxydicarbonatene ble målt ved be-stemmelse av innholdet av aktivt oxygen i provene med gitte mellom-rom. De oppnådde data er oppfort i den folgende tabell: The decomposition rate of the peroxydicarbonates was measured by determining the content of active oxygen in the sample at given intervals. The obtained data is listed in the following table:
Eksempel 7 Example 7
Den folgende' blanding'' ble anvendt ved suspens,'jons-polymerisering av vinylklorid: The following 'mixture' was used in suspension ion polymerization of vinyl chloride:
Det vil sees av tabellen at der ved anvendelse av bis-(^t—tert. butylcyclohexyl)-peroxydicarbonat eller bis-(^--tert.amylcyclohexyl) -peroxydicarbonat i samme molar mengde og i samme tidsrom oppnås hoyere omsetning enn ved anvendelse av diisopropyl-peroxydicarbonat eller dicyclohexyl-peroxydicarbonat. Alternativt kan samme omsetning oppnås i lopet av kortere tid. It will be seen from the table that when using bis-(^t-tert.butylcyclohexyl)-peroxydicarbonate or bis-(^--tert.amylcyclohexyl)-peroxydicarbonate in the same molar amount and in the same period of time, a higher turnover is achieved than when using diisopropyl peroxydicarbonate or dicyclohexyl peroxydicarbonate. Alternatively, the same turnover can be achieved in the course of a shorter time.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8714/66A GB1107956A (en) | 1966-02-28 | 1966-02-28 | Improvements in or relating to organic peroxydicarbonates |
Publications (1)
Publication Number | Publication Date |
---|---|
NO122701B true NO122701B (en) | 1971-08-02 |
Family
ID=9857830
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO167038A NO122701B (en) | 1966-02-28 | 1967-02-27 |
Country Status (13)
Country | Link |
---|---|
US (2) | US3499919A (en) |
AT (1) | AT272302B (en) |
BE (1) | BE693478A (en) |
CH (1) | CH481865A (en) |
DE (1) | DE1618578B1 (en) |
DK (1) | DK120635B (en) |
ES (1) | ES336866A1 (en) |
FR (1) | FR1512825A (en) |
GB (1) | GB1107956A (en) |
IL (1) | IL27376A (en) |
NL (1) | NL6700636A (en) |
NO (1) | NO122701B (en) |
SE (2) | SE361669B (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2151142A5 (en) * | 1970-08-21 | 1973-04-13 | Pennwalt Corp | |
US3879353A (en) * | 1971-09-01 | 1975-04-22 | Owens Illinois Inc | Linear copolymers having pendant peroxycarbonate ester functionality, their synthesis and use |
FR2439794A1 (en) * | 1978-10-26 | 1980-05-23 | Oreal | PROCESS FOR THE PREPARATION OF COPOLYMERS FOR AEROSOL LACQUERS AND AEROSOL LACQUERS CONTAINING THEM |
US4285877A (en) * | 1980-01-17 | 1981-08-25 | Argus Chemical Corporation | Di(2-methyl-2-phenyl propyl) peroxy dicarbonate and other novel (2-alkyl-2-phenyl) substituted peroxy dicarbonates |
FR2475558A1 (en) * | 1980-02-07 | 1981-08-14 | Poudres & Explosifs Ste Nale | PROCESS FOR THE SYNTHESIS OF POLYMERS AND COPOLYMERS BASED ON VINYL CHLOROFORMATE |
DE3038164A1 (en) * | 1980-10-09 | 1982-05-06 | Peroxid-Chemie GmbH, 8023 Höllriegelskreuth | METHOD FOR THE CONTINUOUS PRODUCTION OF DIALKYL PEROXYDICARBONATES |
US4372877A (en) * | 1981-11-05 | 1983-02-08 | U.S. Peroxygen Company | Di(acylperoxy)-1,4-cyclohexane dimethanol-bis-carbonates |
BE1009969A3 (en) | 1996-01-25 | 1997-11-04 | Solvay | METHOD FOR AQUEOUS SUSPENSION POLYMERIZATION OF VINYL CHLORIDE TO dialkylperoxydicarbonates OPERATION. |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2370588A (en) * | 1942-10-22 | 1945-02-27 | Pittsburgh Plate Glass Co | Organic percarbonates |
US2517164A (en) * | 1947-02-19 | 1950-08-01 | Bruno F Arps | Two-speed hydraulic ram |
US2464062A (en) * | 1947-11-26 | 1949-03-08 | Pittsburgh Plate Glass Co | Polymerization with a peroxydicar-bonate catalyst |
NL120371C (en) * | 1959-01-16 | |||
DE1259325B (en) * | 1964-05-22 | 1968-01-25 | Hoechst Ag | Process for the continuous production of solutions of peroxydicarbonic acid esters |
-
1966
- 1966-02-28 GB GB8714/66A patent/GB1107956A/en not_active Expired
-
1967
- 1967-01-16 NL NL6700636A patent/NL6700636A/xx unknown
- 1967-02-01 IL IL27376A patent/IL27376A/en unknown
- 1967-02-01 BE BE693478D patent/BE693478A/xx not_active IP Right Cessation
- 1967-02-10 CH CH198467A patent/CH481865A/en not_active IP Right Cessation
- 1967-02-11 DE DE19671618578D patent/DE1618578B1/en active Pending
- 1967-02-15 ES ES336866A patent/ES336866A1/en not_active Expired
- 1967-02-17 US US616775A patent/US3499919A/en not_active Expired - Lifetime
- 1967-02-23 AT AT180967A patent/AT272302B/en active
- 1967-02-27 SE SE14414/69A patent/SE361669B/xx unknown
- 1967-02-27 SE SE02668/67A patent/SE339940B/xx unknown
- 1967-02-27 NO NO167038A patent/NO122701B/no unknown
- 1967-02-27 DK DK104167AA patent/DK120635B/en not_active IP Right Cessation
- 1967-02-28 FR FR96769A patent/FR1512825A/en not_active Expired
-
1969
- 1969-04-01 US US833229*A patent/US3528956A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
BE693478A (en) | 1967-07-17 |
CH481865A (en) | 1969-11-30 |
US3528956A (en) | 1970-09-15 |
DK120635B (en) | 1971-06-28 |
ES336866A1 (en) | 1968-01-01 |
FR1512825A (en) | 1968-02-09 |
SE339940B (en) | 1971-11-01 |
NL6700636A (en) | 1967-08-29 |
US3499919A (en) | 1970-03-10 |
IL27376A (en) | 1970-09-17 |
AT272302B (en) | 1969-07-10 |
SE361669B (en) | 1973-11-12 |
DE1618578B1 (en) | 1971-01-21 |
GB1107956A (en) | 1968-03-27 |
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